Hell On Heels
by rationalbookworm
Summary: AU. Second prequel to Death of the Devil. The deal with Dean Winchester was important. Too important for just any crossroad demon to take.
1. Introduction

**This isn't really a sequel to Heiress of Illusion, because it's a different storyline, but it's in the same universe and eventually they will come together in another story. I may end up making this a rewrite of season three, but I haven't decided yet. Let me know if that's something anyone out there would be interested in. Until then, enjoy this Intro to Hell on Heels :D**

**Disclaimer: I do not own Supernatural and make no money from writing anything involving the show.**

The King of the Crossroads sat back in his chair. He could feel the summoning. Someone calling for one of his demons. But not just anybody. Dean Winchester. The poor little hunter had lost his baby brother. Now, in a fit of rage and loss, he'd driven to a crossroads and summoned a demon to make a deal. This was too good to pass up.

Normally, for such a high stakes deal, Crowley would go himself, to ensure he got exactly what he wanted. But then he'd be revealing himself to a Winchester. That was never a good idea. Some idiot demons may believe they could best those hunters, but Crowley was smarter than that. No, he couldn't have a face-to-face with a Winchester until he was positive he had no other option.

So who could he trust to send in his place? It couldn't be just anyone, though he was sure many would be eager to make this deal. No. It had to be someone he trusted with his life, because this deal could very well mean just that if something went awry. Well that was easy. There was only two people Crowley trusted with his life. Himself, for starters. And second…

Crowley disappeared from hell and instantaneously reappeared in his castle in Scotland. Hogwarts, a certain resident called it after the first Harry Potter came out in theaters. He didn't often come here, not wanting anyone from hell to know about it, but he had to speak with the only other person who knew about this place, besides the poor souls he had working here who couldn't leave the grounds. Their fault really. They shouldn't have made a deal with him if they couldn't handle the consequences.

Music thumped down the third floor corridor, vibrating the walls and floor and making his head hurt. He stopped outside the large wooden door that lead to the music room and rubbed his temple. He'd never understand why she felt the need to listen to music this loud. How had she not gone deaf yet? With a snap of his fingers, all the noise cut off abruptly, filling the air with an eerie silence.

"Hey!" a feminine voice shouted, followed by the soft padding of footsteps and the door flying open. The petite blonde froze in the doorway, her long hair swinging forward in front of her face. The bottom layer of hair had been died a dark purple. That was new. She was still in her plaid pajama shorts and tank top with bunny slippers on her feet. Her blue eyes lit up when she recognized the man standing in the hall.

"Daddy!" she called, throwing herself at him.

He rolled his eyes and patted her back, "Don't call me that."

She just grinned mischievously, leaning back against the door frame, "I thought you wouldn't be here till this weekend."

"Change of plans. I have a job for you."

"Oh really?" she raised an eyebrow. "You rarely give me jobs. Must be important."

"Oh yes," he smirked. "Plus, I thought you'd like to catch up with the client. It's an old friend of yours after all."

"An old friend?"

"A certain Winchester would like to strike another deal. As you did so well last time, I thought perhaps you'd like another chance."

A grin spread across her face, "I'll go get dressed."


	2. Crossroad Blues Part 1

**(IMPORTANT! I deleted this chapter and reuploaded it so that I could add a section on the bottom. If by some small chance you've actually read this chapter you can skip down to the bottom and just read that. The only real reason I did this was so the next chapter can be solely Dean's deal with the demon. Sorry for any confusion.)**

**First, whenever I do a full rewrite of an episode, at least for this fandom, I'll probably split it in two. It's just easier for me that way.**

**Second, The intro takes place just before Dean makes the deal to save Sam after he dies at the end of season 2, but I needed to lay a little back story first, so we're starting with Crossroad Blues. One of my favorite episodes :D**

**Third, I didn't edit this before posting, so please excuse any mistakes. If there's any major ones that absolutely need to be fixed, please let me know. Thanks so much :)**

**Fourth, I've started reworking my Harry Potter story, something I first began way back in junior high (so about ten years ago) and have since changed a billion times. I'm actually really liking it so far though. Anyway, my point is, with this story as well as my other four, idk how often I'll post. Especially if I decide to start posting my HP, which is a huge possibility. Hope you don't hate me for that.**

**Without further ado, here's Part One of Crossroad Blues!**

Pulling to the side of the road outside of the run down shack, Sam and Dean stepped out of the car. Dean rolled his shoulders, relieving the tension building there. Ever since they started this case, something had been niggling at the back of his mind. Something was off and he couldn't tell what. It was bugging the crap out of him. He glanced over at Sammy, seeing the taller man eyeing the building with suspicion. Nothing wrong there. Maybe it was just him.

He sighed, moving forward with his brother. They both looked around out of habit. _Always check the area_, his dad's voice rang through his head. _Never go in blind or cocky. _He shook his head slightly, not wanting to hear that voice right now. It was just too much, even for him.

A spot of bright yellow in the otherwise dead vegetation caught his eye, making him stop and tilt his head in confusion. "Hey," he halted Sam.

"Yeah?"

He motioned to the little flowers he saw growing all around the crossroads the stood by, "That's weird."

"What?" How was he the smart one again?

"Think someone planted these?" he asked, trying to keep the sarcasm out of his voice. They walked to the nearest corner to have a closer look

"In the middle of all these weeds?" Well, he was catching on.

"These are, uh, what-do-you-call-'em?"

"Yarrow flowers." That's more like the encyclopedia of weird shit he knew and loved.

"Yeah." He'd definitely heard of those before. "Used for certain rituals, aren't they?"

"Yeah, actually, summoning rituals."

"Huh." He turned to look at the crossroads. If this were a cartoon, a light bulb would have just gone off over his head. "So, two people become sudden successes about 10 years ago, right around the time they were hanging out here at Lloyd's."

"Where there just happens to be a crossroads. You think?"

"Let's find out." Dean marched purposefully to the middle of the crossroads, turning in the spot to mentally measure out how far he was from each corner where the flowers grew. "This seem about the dead center to you?"

Sam shrugged.

"Go get the shovel," he ordered, waving him off. He watched his not-so-little brother roll his eyes and stomp back to the trunk. Dean grinned, glad to see that no matter how much things changed, Sammy would still be Sammy and still hate to be the 'pack mule'. Dean liked to tease him, saying he was much more like a dog, fetching things he needed. That only ever got him one of Sam's bitch faces. Number twelve, if he remembered correctly.

Sam came back and shoved the shovel into his brother's chest, making him grunt. Dean rolled his eyes at the younger man's smirk before leaning down and digging a relatively small hole. At least he wouldn't have to dig very deep. In a matter of minutes he heard metallic thunk and looked up with a smirk, "Yahtzee."

He dropped down, digging the rest of the way with his hands. He didn't mind doing this seeing as Sam still had his right hand in a cast from that Zombie-thing. At the bottom of the hole he found a small metal box, slightly rusted and caked in mud. He yanked the top open to inspect the contents, grimacing at what he found. He picked up and old bone, hoping it wasn't a human finger or anything like that as Sam reached over with his good hand to sift through the rest.

The younger brother pulled out a glass bottle filled with black sand, "I'd be willing to bet that's graveyard dirt. And a black cat bone."

Dean turned away, dropping the bone back into the tin box, "That's serious spell work. I mean, that's Deep South hoodoo stuff."

"Used to summon a demon."

"No just summon one," he sighed, flipping the lid closed as he stood and turned to glance at the bar, "Crossroads are where packs are made. These people are actually making deals with the damn thing." The disgust in his voice couldn't have been clearer. "You know, cuz that always ends good."

Sam had stood up as well, his deep-in-thought face in place, "They're seeing dogs, all right. But not black dogs, they're seeing hellhounds. Demonic pit bulls."

"And whoever this demon is, it's back and it's collecting. That doctor lady, wherever she's running, she ain't running fast enough."

Dean watched Sam's jaw clench as he glanced around, as if he would be able to spot the thing. He mentally cursed. He knew that face. He knew what was coming. And he knew he wasn't going to like it.

Sam was still thinking as they walked back to the car, trying to put everything together, "So it's just like the Robert Johnson legend right? I mean, selling your soul at the crossroads kind of deal?"

Dean turned to face him, "Yeah, except that wasn't a legend. I mean, you know his music."

Sam half shrugged, glancing away with a frown.

"You don't know Robert Johnson's songs? Sam, there's occult references all over his lyrics. I mean: 'Cross Road Blues,' Me and the Devil Blues,' 'Hell Hound on My Trail'?

Sam just looked confused.

Dean sighed, "Story goes that he died choking on his own blood. He was hallucinating and muttering about big, evil dogs."

"Now it's happening all over again."

"Yeah."

"We gotta find out if anyone else struck any bargains here." And there it was. The one thing he knew was going to happen and that he hated. Sam really needed to learn not to try to save everyone. Some people just weren't worth saving. Especially these. They asked for this.

"Great," he muttered. "So we gotta clean up these people's mess for them? I mean, there not exactly squeaky clean. Nobody put a gun to their head and forced them to play Let's Make a Deal."

"So what? We just leave them to die?"

"Someone goes over Niagara in a barrel you gonna jump in and try to save them?"

"Dean," Sam shook his head.

Sighing, he looked down, composing himself. He knew the moment he realized what was happening Sam wouldn't let this go, wouldn't just walk away. He nodded once, "Alright. Fine. Rituals like this, you gotta put your own photo into the mix, right?" He held up a small, wrinkled black and white photo from the box, "So, this guy probably summoned the thing. I'll go see if anyone inside knows him. If he's still alive."

He walked away towards Lloyd's, not wanting to argue with his brother anymore. He knew he was being harsh, but Sam's insistence on trying to save everyone, even those who don't deserve it, could sometimes be grating on his nerves. He needed a second to calm down before they hunted up whoever summoned a deal-making demon.

* * *

The large apartment building may have once been very nice looking, the red brick and white trim crisp and neat. Now, however, it looked old and rundown, dirty with trash piled in front by the road. The front door was closed but unlocked, allowing them easy access. Together, the brothers climbed up the steps slowly, always aware of their surroundings, expecting anything to happen.

"What's the guy's name again?" Sam asked, annoyingly not out of breath as Dean huffed up yet another flight stairs. Damn old buildings with no elevator.

"George Darrow. Apparently quite the regular at Lloyd's. His house probably ain't up next on _MTV Cribs_, is it?" He glanced around at the dirty, trashed floor below and the equally wrecked floor they were approaching.

"Yeah," Sam huffed out a fake laugh at his brother's version of humor. "So, whatever kind of deal he made…"

"It wasn't for cash," Dean finished. "Oh, who knows? Maybe his place is full of babes in Princess Leia bikinis?" He smirked at Sam as the younger man rolled his eyes and shook his head in disgust. "I'm just saying, this guy's got one epic bill come due. Hope at least he asked for something fun."

They finally reached apartment 4C, both falling silent as Dean stared up at the black lettering on the door.

"Look at that," Sam pointed to the ground, drawing Dean's attention.

A line of black powder was spread across the bottom of the door, much like how they used salt to keep out demons. The older Winchester crouched down and gently scooped up a bit of the powder on his finger tip. He sniffed it to see if he could identify it, coming up with nothing he recognized.

"What is that, pepper?" he asked Sam.

The door creaked open, making them jump to their feet to find an old, gray haired black man who looked just as ragged and decaying as the building he lived in. He eyed the two boys with suspicion, not moving from the small crack he opened with the door.

"Who the hell are you?" he asked in a raspy, deep voice.

"George Darrow?" Dean checked, though he was relatively sure it was the right man.

"I'm not buying anything," the man said quickly, pushing the door to slam it shut.

Dean placed his hand on the door, talking to distract him enough to perhaps let them in, "Looks like you went for the wrong shaker, there." He motioned to the line of black powder, "Usually when you wanna keep something evil out, you go for the salt."

George's eyes shifted between the two men, "I don't know what you're talking about."

"Talking about this," he pulled the old picture from the box out of his pocket and held it up for George to see. The man's eyes widened slightly in shock and a little fear. "Tell me," Dean continued. "You see that hellhound yet?"

"Look," Sam jumped in with his soft, calming tone, seeing the man ready to slam the door in their faces again. "We wanna help. Please. Just five minutes."

Slowly, not taking his eyes off the boys, the man backed away, leaving the door open as he turned toward a table in the middle of the room. Cautiously, the brothers entered, looking around. Skulls, bottles holding various substances, all the typical hoodoo stuff was visible as well as an easel and piles of paintings stacked against the wall. Blues music was playing on a record player in the corner. Dean raised an eyebrow at the odd assortment of items but didn't comment. George stood with his back to them, pouring himself a drink. Dean couldn't blame him. He'd drink too if he knew he was going to die soon. Hell, he drank copiously anyway.

"So what is that stuff out front?" Sam asked curiously.

"Goofer dust," George answered shortly. He took a drink, eyeing their confused expressions, "Oh you boys think you know something about something but not goofer dust?" He shook his head, reaching for a plain brown sack that he tossed easily to Dean who caught it one handed.

"Well, we know a little about a lot of things," Dean shrugged, looking into the bag to find more of the slightly sparkly, black dust. "Just enough to make us dangerous."

George looked unimpressed.

"What is it?" Sam asked, covering for his brother's dramatic way of speaking.

"Hoodoo. My grandma taught me. Keeps out demons."

Dean nodded, "Demons we know."

"Well then, keep it," he moved passed them with his glass, a rag covered in paint, and a few paintbrushes. "Maybe it'll do you some good. Four minutes left."

"Mr. Darrow," Sam stepped forward, using his soft voice again. "We know you're in trouble."

"Yeah, that you got yourself into," Dean griped, making it clear how he felt about it.

Sam shot him a look, "But it's not hopeless, alright? There's gotta be something we can do."

"Listen," George sank down into an armchair, alcohol still in hand. "I get that you boys wanna help. But sometimes a person makes their bed and they just got to lie down in it." Dean silently agreed. Maybe George Darrow wasn't so bad after all. "I'm the one that called that demon in the first place."

"What you do it for?" Dean asked, smirking a bit. Nothing in the house looked like something someone would make a deal for.

"I was weak. I mean, who don't wanna be great? Who don't want their life to mean something? I just – I just never thought about the price."

"Was it worth it?"

"Hell, no. Of course, I asked for talent. Should have gone for fame. I'm still broke. And lonely. Just now I got this pile of paintings don't nobody want. But that wasn't the worst."

"Go on," Sam urged when the old man hesitated.

"Demon didn't leave," he shook his head, his eyes sad. "I never counted on that. After our deal was done the damn thing stayed at Lloyd's for a week just chatting, making more deals. I tried to warn folks, but who's gonna listen to an old drunk?"

"How many others are there?"

"This architect, a doctor lady," both of which they already knew about. "I kept up with them. They been in the papers. At least they got famous."

"Who else, George?" Dean stepped forward. "Come on, think."

"One more. Nice guy too. Hudson. Evan, I think. I don't know what he asked for. Don't matter now." His smile was a little bitter, "We done for."

"No." Sam shook his head. "No, there's gotta be a way."

"You don't get it. I don't want a way."

"Look, you don't have–"

Sam was cut off as George stood, "I called that thing! I brought it on myself. I brought it on them. I'm going to hell, one way or another. All I want is to finish my last painting. A day or two, I'm done. I'm just trying to hold him off till the end. Buy a little time." He turned away, setting down his glass and gathering his paint material, "Okay, boys. Time you went. Go help somebody that wants help."

"We can't just–"

Sam was cut off yet again, "Get out! I got work to do."

"You don't really wanna die," Sam said incredulously.

George spun around to glare at him, "I don't? I'm…I'm tired." He turned away again, dismissing them as he continued on his painting. Dean watched him for a moment. As much as he was all for the 'let them lie in their bed' thing, it was sort of heart wrenching seeing the man so broken down like that. All the while something kept cropping up in the back of his mind, telling him this was all hauntingly familiar in some way, though he was sure he'd never had a case quite like this before. He glanced at Sammy and nodded toward the door. Sam sighed and turned to follow him out.

* * *

Later that night, after stopping to grab a bite at the local fast food place, Sam and Dean trotted up the front steps to Evan Hudson's nice suburb home. The lawn was mowed, the hedge was trimmed, everything was quiet and peaceful. And Evan Hudson was going to die tonight unless they found a way to stop the deal.

Sam used his good hand to knock loudly on the door. A few minutes later the door swung opened revealing a small, panicked looking man with dark shadows under his eyes who stood straight, trying to not look frightened. Oh, this was definitely Evan Hudson.

"Yes?" he asked steadily.

"Evan Hudson?" Sam clarified.

"Yeah."

"You ever been to a bar called Lloyd's?" Dean asked. "Would have been about ten years ago?"

The panic he'd been trying to suppress flashed across his face as he grabbed the door and slammed it closed, locking it. Dean could hear his rapid footsteps retreating.

"Come on," he called. "We're not demons."

Sam turned to him, giving him one of his bitch faces, "Any other bright ideas?"

Dean stepped back, swinging one leg up so he could kick out. The heel of his boot landed just below the doorknob, the door swinging open on impact. That lock was terrible. Way too easy to break through. They entered the house, following the sound of footsteps and a door opening and closing. Two double doors down the hall seemed to be the right place. Dean stepped back again, raising his foot to kick down the next door. He was on a roll tonight. Only for Sam to catch his leg, bitch face in place once more as he reached out and pressed the door handle down. It opened without protest and Dean shrugged. His way was more fun. They cautiously went in, not wanting the dude to lash out and attack them.

"Evan?" Sam called softly.

"Please." Dean did not jump as Evan popped out from behind a shelf with his hands raised in surrender. "Don't hurt me."

"We're not gonna hurt you, alright?" Sam raised his hands too, showing he held no weapon. Of course, he had his gun tucked in his waistband, but Evan didn't need to know that. "We're here to help you."

"We know about the genius deal you made," Dean was much less sympathetic.

"What? How?"

"It doesn't matter," Sam shook his head. "All that matters is we're trying to stop it."

"How do I know you're not lying?"

"Well, you don't," Dean smirked. "But you're kinda low on options there, buddy boy."

Evan swallowed hard and nervously began to pace, "Can you stop it?"

"Don't know," Sam shrugged. "We'll try."

"I don't wanna die."

"Of course you don't." Dean scoffed. "Not now."

"Dean. Stop."

"What'd you ask for anyway, Ev? Huh? Never need Viagra? Bowl a perfect game? What?"

Evan crossed his arms defensively, "My wife."

Dean laughed humorlessly, "Right. Getting the girl. That's worth a trip to hell for."

"Dean. Stop."

"No," Evan looked up, angry now. "He's right. I made the deal. Nobody twisted my arm. That…woman…or whatever she was, at the bar – she said I could have anything I wanted. I thought she was nuts at first, but…" he sighed. "I don't know, I was…I was desperate."

Dean felt his stomach begin to drop. This could be a 'get the girl' deal, but his tone of voice made it sound different somehow. That difference was making his gut twist, that feeling in the back of his mind was back but he still couldn't place it. All he knew was that all this felt too, too familiar.

"Desperate?" Sam prompted.

Evan looked away with an exhausted sigh, "Julie was dying."

Dean frowned. No. Nonononono. Please, don't let it be that. "You did it to save her?" Save her. It was for her. But it wasn't. Just like with his dad. That was the familiar feeling. His dad had died, right after he miraculously came back via the yellow-eyed demon. But that couldn't be it. John Winchester would never deal with a demon, right? But then again, this family always put each other first. John had been the one to teach them that.

"She had cancer," Evan was saying, distracting Dean only minimally. "They stopped treatment; they were moving her into hospice. They kept saying: 'a matter of days.' So yeah, I made the deal. And I'd do it again. I'd die for her on the spot."

Something in Dean snapped and he couldn't hold in his thoughts anymore, directing it more at his dead father than Evan, "Did you ever think about her in all this?"

"I did this for her."

"You sure about that? I think you did it for yourself. So you wouldn't have to live without her. But guess what, she's gonna have to live without you now. And what if she knew how much it cost? What if she knew it cost your soul? How do you think she'd feel?"

"Okay. That's enough," Sam stepped forward, pulling Dean back. "Evan. Sit tight, alright? We're gonna figure this out."

Dean turned and walked out of the room, unable to really breathe in there he was so mad. How could his father do this to him? How could he think this was alright?

"You alright? Sam followed him out.

"Why wouldn't I be?" He shifted to face his brother, not bothering to put on a neutral expression. Sam already saw how he'd been in there. He probably already had everything figured out, all the thoughts roiling around the older Winchester's mind. He took a deep breath, changing the subject quickly before he got too mad and took it out on Sammy instead, "Hey I got an idea. You throw George's hoodoo at the hellhound. Keep it away as long as you can. I'll go to the crossroads, summon the demon."

"Summon – Are you nuts?"

"Maybe a little. But I can trap it. I can exorcise it and I can buy us time to figure out something more permanent." The plan was half-baked at best, but it was the only thing he could think of on the fly like this. And he needed something, anything, to keep him distracted from his anger and hurt right now. He didn't need any of that chick flick shit.

"Yeah, but how much time?"

"A while. It's not easy for them to claw their way back from hell into the sunshine."

Sam shook his head, "No. No way."

"Not allowed to say no, Sammy. Not unless you got a better idea."

"Dean, you can forget it, alright? I'm not letting you summon that demon."

"Why not?" He braced himself for what he knew was coming. Sammy's attempt at a chick flick moment. Dammit. Why'd the kid always have to do this? Couldn't they just move on and hope it goes away?

"Because I don't like where your head is at right now, that's why not."

"What're you talking about?"

"Dude, you've been on edge since we found that crossroads, Dean, and I think I know why."

Time to deflect, "Well, we don't have time for this." He tried to move past and walk away, but Sam wasn't giving up.

"Dad. You think maybe dad made one of these deals, huh? Hell, I've been thinking it. I'm sure you've been thinking it too."

Dean hesitated, at war with wanting to run away with his feeling and knowing Sam would probably just hunt him down and sit on him or something to make him talk. Finally he said softly, "It fits, doesn't it? I'm alive, dad's dead. Yellow-eyed demon was involved. What if he did? What if he struck a deal? My life for his soul?"

Dean had never been more grateful to a demonic presence as Evan interrupted, "I think I hear it. It's outside."

"Just keep him alive, okay?" he growled.

"Dean–" Sam began to argue again

"Go!" he called, already halfway to the door. Enough chick flick. They had a job to do.

* * *

**That has got to be THE longest chapter I have ever written. Hope you like it. Part 2 should be up soon.**


	3. Crossroad Blues Part 2

**Again, I didn't take the time to edit. I'm just too lazy today, I guess.**

**If you didn't notice I briefly deleted the last chapter to add more to the bottom. Pretty much the entire meeting with Evan has been moved from this chapter to that chapter. So if you haven't read that, you might want to. **

It didn't take long to set up the trap and dig up George's summoning box from the trunk of the Impala. Then all he had to do was rip his picture off of one of his old fake IDs and throw it in the mix. He buried it back where he had dug it up and waited. He wasn't sure how long it took for them to come, but it couldn't be long.

"So," a feminine voice had him spinning around. A young beautiful woman with long dirty blonde hair and bright blue eyes smiled at him. She wore a knee length black cotton dress that plunged low on her neckline and strappy heels. "What brings a guy like you to a place like this?" she teased. When he didn't answer she smiled again. "You called me?"

"I'm just glad it worked,' he admitted.

"First time?" she kept up the teasing edge of her voice, though now that he wasn't surprised by her sudden appearance he noticed it didn't quite match…her. The voice was slightly low toned, a little husky. Looking at her he would imagine her voice to be lighter, more carefree. Then again the poor girl had a demon inside her controlling her every move. How was he to know if this was how the person the body really belonged to sounded like?

"You could say that," he answered, seeing she wanted him to speak.

"Oh, come on, now," she slowly walked over the gravel road towards him, gracefully stalking forward like a panther until she was directly in front of him, only a foot of space separating them. "Don't sell yourself short." Her eyes shifted from sparkling blue to blood red and back as she spoke, "I know all about you, Dean Winchester."

"So you know who I am?"

"I get the newsletter."

"Well, don't keep me in suspense." He knew he should make this quick, Evan's life depended on it, but he couldn't help but be curious. He inched closer, using his size to try to intimidate her. It didn't always work, but he could try. She smiled up at him, clearly not affected. "What have you heard?"

"Well," her eyes traveled up and down his body, making an odd warmth flow through him. What the hell was that? "I heard you were handsome but," she moved closer to whisper playfully, "You're just edible." She smiled again. "What can I do for you, Dean?"

He glanced around, acting it up a bit, "Maybe we should do this in my car. Nice and private."

"Sounds good to me," she took a step back, moving towards the Impala without taking her eyes off him. She linked her arm through his as he guided her down the road. Her hand on his forearm was warm, sending little shock waves through him. Seriously? He could _not_ be attracted to this bitch. This was a demon for God's sake! His only comfort was that perhaps he was merely attracted to the meat suit she was traveling in. Yeah, that had to be it.

"So I was hoping we could strike a deal," he commented to distract himself.

"That's what I do," she quipped.

"I want Evan Hudson released from his contract."

She gave a half smile and shook her head slightly, "So sorry, darling. That's not negotiable."

"I'll make it worth your while," he gently dropped her arm as they reached the car, turning to face her.

"Oh really? What are you offering?" she moved into his personal space, tilting her head back to keep eye contact while revealing a startling amount of cleavage from his point on view.

He swallowed, "Me."

"Well, well, well. You'd sacrifice your life for someone else's? Like father, like son."

He stumbled back half a step at those words, but regained his compose quickly, hand reaching out to rasp onto something to ground him. His fingers curled around the handle for the passenger door on the Impala.

She followed after him, into his personal space once more, "You did know about your dad's deal, right? His life for yours? Now, I didn't make the deal myself, but, boy, I wish I had."

Dean forced himself to smile slightly, yanking the door open, "After you."

"Such a gentleman," she smiled before looking down to watch where she was going. She froze and he silently cursed. Time for plan B. When she looked up, her eyes were completely red again, this time not shifting back. "A devil's trap?" she growled angrily. "You've got to be kidding me." She shoved the door closed, making the whole car rattle with the force.

"Hey, watch it!" he nearly shouted instinctively.

"You stupid, stupid–" she edged closer to him, making him stumble back in alarm. He'd never seen a demon's eyes stay that color. Normally they shifted back to the human's natural eye color. But hers were not only still red, but glowing slightly. "I should rip you limb from limb."

"Take your best shot," he tried to sound like his cocky self, but inside he was more than a little worried. This was completely new and he didn't know how to react to it. Worse yet, a tiny part of him was kind of turned on by the power radiating from her small frame.

Suddenly she stopped advancing on him, giving him a calculating look, "No. I don't think so. I won't put you out of your misery."

"Yeah? Why not?"

"Cuz your misery's the whole point. It's too much fun to watch. Knowing how your daddy died for you. How he sold his soul. I mean, that's gotta hurt." She began a slow approach again, backing him up to the water tower. Good. Perfect. He kept his face a mask of hurt and anger, which really wasn't hard considering the circumstances. "You wake up and your first thought is, 'I can't do this anymore'. You're all lit up with pain. I mean, you loved him so much. And it's all your fault." She chuckled, "You blew it, Dean. I could've given you what you need."

"What do I need?"

"Your father. I could have brought him back." She sighed, backing away, "Your loss. See ya, Dean. I wish you a nice, long life."

She turned away without a backwards glance, walking around the water tower. He ducked under it, watching her go for half long moment. He let all his emotions he kept bottled up leak into his voice when he called after her, "Hold on."

She stopped, her head cocked to the side to show that she was listening. She turned when he didn't say anything and he kept his head bowed, watching from the corner of his eye as she sighed and turned back around.

"You're lucky I've got a soft spot for lost puppies and long faces." He looked up, giving his best lost puppy expression as she leaned against one of the beams, "I just can't leave you like this. Besides, you didn't call me here to bargain for Evan. Not really."

"Can you bring him back?" his voice was still rough with emotion. "My dad?"

"Of course I can," she said as though talking to a child who asked her to fix a broken toy. "Just as he was. Your dad would live a long, natural life like he was meant to. That's a promise."

"What about me?"

"I could give you ten years. Ten long, good years with him. That's a lifetime. The family can be together again. John, Dean, Sammy." Hey, no one got to call him Sammy, but him. "The Winchester boys all reunited." He made a show of trying to decide what to do, looking away. She moved under the tower with him, just as he wanted, and got back into his space. Laying a hand on his arm, she tilted her head up to look at him. Her eyes were still red, but no longer glowing. "Look, your dad's supposed to be alive. You're supposed to be dead. This will just set things straight. Put things back in their natural order. And you get ten extra years on top. That's a bonus."

He nodded slowly, looking down at her only to realize that put their faces inches apart. He had to back off before she kissed him, sealing the deal before he could finish what he intended. He casually moved away, as though pacing as he thought, until he was outside of the shadow of the water tower.

"Do you think you could," he paused, turning to face her, "Throw in a set of steak knives?" he smirked.

She chuckled, "You know, the smart ass, self-defense mechanism of yours–" she stopped abruptly, freezing on the edge of the water tower, her face scrunching in what appeared to be pain. Her head slowly tipped back until she spotted the large devil's trap he had drawn on the underside of the water tower.

"Dean," she warned.

"Now you're really trapped," he teased. "That's gotta hurt."

"Let. Me out. Now."

"Sure. We just gotta make a little deal here first. You call off your hellhound, let Evan go. Then I'll let you go."

"I can't break a binging contract."

"Hm. And by 'can't' you mean, 'don't want to'?" he raised his eyebrows. "Last chance. Evan and his wife get to live to a ripe, old age. Going…going…"

"Let's talk about this."

"Okay. Gone." He reached into his inside coat pocket and pulled out his father's journal, flipping casually through the pages till he found what he wanted.

"What are you doing?" she demanded nervously

"You're just gonna go on a little trip. Way down south," he looked up to smirk at her. Her eyes had turned back to blue and he saw no small amount of fear in them. Strange. While most demons hated being exorcised, what with the pain and being sent to hell and all, none of them had ever been sincerely terrified like she seemed to be. Why had this one been so different than the hundreds of others he'd dealt with in the past? He shook his head, dislodging the though as he began reading, holding out a rosary.

"Look, forget Evan," she begged before he could say a word. "Think of your dad."

He glared up at her, turning away as he read the first line. He continued on sometimes glancing up see her slowly doubling over in pain. He was almost startled. Normally demons twitched a lot, got thrown about a bit. But none of them had ever sunk to the floor clutching their stomach, which was exactly what she was doing. It just looked so…so _human._ It was worse when she looked up, blue eyes shining as tears streaked down her face, blood pooling at the corner of her mouth. What the _hell_?

"Wait!" she finally choked out, coughing up blood as he froze. He watched, completely gobsmacked as she rose shakily to her feet, wiping blood off her lips with the back of her hand. Her entire body was trembling as she stumbled forward and grasped the lapels of his jacket before he could even flinch. "You have a deal."

She fell forward, forcing her lips on his. One of his hands automatically reached up to cup the back of her head, tilting it back so he could deepen the kiss while the other dropped the journal and wrapped around her waist, keeping her upright. He could taste the coppery human blood still lingering there. Slowly he pulled away, taking a deep breath to compose himself. He would never admit it, but he had never had a kiss that had lit his entire body up that quickly. He cleared his throat stepping back fully out of her reach as she smirked at him. Quickly he snatched up the journal and rosary, if only for an excuse not to look at her. Why did he suddenly feel like a virgin teen again?

"What the hell was that for?" he knew he should know the answer to that. He felt like he did, but his mind still felt like a jumbled mess.

"Sealing the deal," she answered still smirking as she wiped away the last bit of blood.

"I usually like to be warned before I'm violated with demon tongue."

She laughed lightly, "Only, honey. That wasn't demon tongue."

"Right. It's your meat suit's tongue."

"Who ever said I was wearing a suit?" She raised an eyebrow but didn't clarify, changing the subject instead, "Evan Hudson is free. He and his wife will live long lives."

He forced himself to focus on what was important. He could always have Sam or Bobby, the research geniuses, to look up what the hell she was talking about. "How do I know you're not lying?"

"My word is my bond."

"Oh really?"

"It is when I make a deal. It's the rules. You got what you wanted. Now let me go."

He moved away, looking at the book in his hand as the other fiddled with the rosary. He didn't actually intend to send her back. He could be a jackass but he didn't often break promises either. No, he just wanted to find out what she had meant earlier about the meat suit. But he had a feeling she wouldn't be very talkative after all that.

"You're gonna double-cross me?" she asked incredulously when he didn't immediately let her out. "Funny how I'm the trustworthy one."

He shrugged. Maybe if he scared her enough she'd let something slip.

She leaned forward precariously on her heels, arms reached out to lean on two beams, "You know, you renege, send me to hell," he voice broke slightly, "sooner or later I'm gonna climb out and skinning Evan Hudson will be the first thing I do." He eyes held a little red in them as she talked, making her threat seem very real.

He nodded, tucking his things away before climbing up the side of the water tower. He reached one of the looser boards above him and yanked down, breaking the line on the trap. She sighed, stepping away from the tower. She paused in the middle of the road to slip out of her shoes, holding them in one hand. She glanced up as he hopped back down to the ground. Face to face once more under the moonlight, he saw she had a fine coat of sweat on her brow and she looked paler than before, her hands still trembling slightly. He'd never seen a demon react to an exorcism like that.

"I gotta tell you," her voice held a lot more bite than it did when they started. "You would have never pulled that stunt if you knew."

"Knew what?"

"Where you dad is. You should have made that deal. See, people talk about hell, but it's just a word. It doesn't even come close to describing the real thing."

"Shut your mouth, bitch."

"If you could see your poor daddy, hear the sounds he makes because he can't even scream."

"How about I send you back?" He stepped forward, hoping to care her away. It worked, but not in the way he thought it would. He'd seen demon's leave bodies before, seen the black smoke rush out of their mouth as the human screamed. That didn't happen here though. His hand had been about to grab onto the demon's arm, only to be grasping thin air. Or rather, black smoke. He stumbled back in shock, his jaw hitting the ground. The black smoke was identical to any other demon's except that she was literally _turning into smoke_. He blinked, thinking perhaps he was seeing things. But the image would go away until the smoke finally flew up and disappeared into the night.

* * *

**So this is a lot shorter than the last chapter. At first I was just trying to make them even but then decided, screw it. The deal deserves it's own chapter. Anyways, at least you got it on the same day, right?**


	4. One Year

**Again, not edited. Partly because I didn't edit the other chapters either, but mostly because it's two in the morning and i'm tired. This one is based off the last episode of season two, but since I'm didn't rewrite the whole thing I decided not to call it All Hell Breaks Loose. This _is_ the last chapter to this story, but it will continue in another. Just give me some time to get it all together. I'm still not sure if I want to write one more prequel or just start the big main storyline. Anywho, enjoy the end of Hell on Heels!**

He felt nauseous. He felt…he couldn't even name all the things he felt. The pain was so utterly all consuming. He couldn't breathe. He couldn't think. He couldn't do anything but stare. Stare at Sammy, lying on a cot in some abandoned building – the only place he could make it while lugging the big guy. He looked like he was sleeping. God, Dean wished he that was it.

The front door opened, preceding Bobby's call for him. He hardly twitched. He knew what was coming. The lecture about pulling himself together, getting his brother a proper funeral. But he couldn't He _couldn't_ do it. Not for Sammy. Not his baby brother. This was a million times worse than when their dad died. There had to be another way. He had to bring his brother back. No matter the cost.

He finally turned as Bobby walked in, holding up a bucket of chicken, "Brought you this back."

He swallowed around the lump in his throat, the one he'd been fighting since he held his brother and watched him die. He had to work through this if he was going to get his brother back.

"No thanks. I'm fine," he answered gruffly, listening to Bobby shuffle around the room behind him.

"You should eat something." Bobby, always the concerned parent. He'd been a hell of a father figure for him. But now wasn't the time for that.

"I said I'm fine." Dean turned fully around, picking up a bottle of Jack as Bobby frowned at him.

"Dean. I hate to bring this up, I really do." And here it comes. "But don't you think maybe it's time we bury Sam?"

Dean raised his head to give his pseudo-uncle a stern look, "No."

"Well, we could maybe–"

"What, torch his corpse?" he cut off harshly. "Not yet."

Bobby leaned forward, looking more serious than Dean had ever seen him, "I want you to come with me."

"I'm not going anywhere."

"Dean, please."

"Would you cut me some slack?"

"I just don't think you should be alone, that's all. I gotta admit I could use your help. Something big is going down. End-of-the-world big."

"Well, then let it end!" Dean finally snapped, yelling at Bobby as tears filled his eyes again. It was annoying how much he had cried lately, how much he still felt like crying.

"You don't mean that."

He pushed up from his chair, knocking it back as he strode around the table, getting in Bobby's face, "You don't think so? Huh? You don't think I've given enough? You don't think I've paid enough? I'm done with it. All of it. If you knew what's good for you, turn around and get the hell out of here." Bobby just stood there, looking shocked that Dean would say those things. It only served to piss Dean off more. He didn't want Bobby around for the things that were floating around in his head. He felt guilty enough as is. But he just wanted his brother back, God damn it! "Go!" he shoved Bobby away, hoping he'd get the hint. The hurt look on the older man's face, however, had him pulling back, reigning in his anger. "I'm sorry. I'm sorry." He turned away again. He just couldn't face bobby anymore. "Please, just go."

Bobby moved to the door hesitantly, "You know where I'll be."

Dean sighed once the front door slammed closed. His thoughts all headed down the same path, one he knew Sam would be pissed with him for, but he had to do it, and he had to be alone to prepare.

It was dark by the time he was ready, and yet he couldn't seem to leave Sam's side. He sat in a hard desk chair, studying his brother's peaceful face and trying to think of what he would say to Sammy if he could hear him. How to explain why he was going to do what he was going to do?

"You know, when we were little and you couldn't have been more than five and you started asking questions. How come we didn't have a mom? Why do we always have to move around? Where'd dad go? He'd take off for days at a time. I remember I begged you, 'Quit asking, Sammy. Man, you don't wanna know.' I just wanted you to be a kid. Just for a little while longer. I always tried to protect you. Keep you safe. Dad didn't even have to tell me. It was just always my responsibility, you know? It's like I had one job. That one job. And I screwed it up. I blew it. And for that, I'm sorry."

He stopped, his lips trembling as tears leaked out from under his lashes. He leaned forward, elbows on his knees, and clenched his hands in an attempt to steady himself. He failed miserably. He sighed, rubbing at his eyes with one hand, "I guess that's what I do. I let down the people I love. I let Dad down. And now, I guess I'm just supposed to let you down too? How can I? How am I supposed to live with that? What am I supposed to do? Sammy. What am I supposed to do?" He stood up, anger building up again at the thought. He just felt so frustrated with himself. With life. "What am I supposed to do!"

Without a second thought, he grabbed everything he needed, tossed it into the trunk of the Impala and hopped in. He'd already scouted the perfect place earlier, before his fight with Bobby. Then it had been a "just in case", or at least that's what he told himself. He really didn't want to admit that he had been planning this since Sam breathed his last breath. He may have been against this when it was for him. But this was Sammy. That changed everything.

He jerked to a stop on the side of the road and went back to the trunk, throwing together all the little pieces that had scattered into a small tin box, much like the one he had used last time he did this. The memory made him pause. Would it be like last time? Would he get the same mysterious demon or a more normal one? No time like the present to find out, he supposed.

Slamming the trunk closed, he marched down the road to the crossroad, checking to make sure it was the dead center before kneeling down and burying the little box. He stood back up, dusting off his hands absently as he looked around, waiting. Waiting too long, "Oh, come on already. Show your face, you bitch!"

"Easy sugar, you'll wake the neighbors," a hauntingly familiar voice commented from behind him.

He spun around, coming face to face with the same freaky demon as before. She wore another low cut, curve hugging black dress, but replaced her heels for gladiator sandals. Her blonde hair was down, flowing over her shoulders in waves, now sporting dark purple dye on the bottom layer.

She smiled, blue eyes sparkling, "Like it?" She motioned to her hair. "Just got it done."

He didn't say anything, not really in the mood for small talk or jokes.

"No then?" she shrugged. "I must say, it is so, so good to see you. I mean it. Look at you." She moved closer getting into his personal space again. Her smile was turning into a smirk. He could almost hear the snarky comments beginning to fly. He gritted his teeth, bracing himself for her to prod at the open wound that was Sam's death.

But then she faltered. The smirk slid off her face as she tilted her head in curiosity, concern lighting her eyes. A hand reached up, lightly cupping his cheek and forcing him to look down at her.

"Your family's dead," her voice held none of the teasing he expected. Oddly enough, he caught more than a little sympathy however. "I'm sorry."

Snarky demons, he could deal with. Assholes, pricks, douches. Fine. Whatever. All in a day's work. But this? An understanding demon? As if their last encounter hadn't been enough to rattle his cage. Why was this one so different? What was wrong with her? Or what was right?

She dropped her hand and moved back, sliding back into the playful, bitchy flirting like she was simply changing clothes, "Following in Daddy's footsteps." She grinned and he realized, this was all a show. A show for him so he wouldn't have to deal with Sam's death like a normal person. He could take it out on her with banter and threats, save his brother, and be on his way. Why? Why was she doing this? What the hell was going on? "You wanna make a deal. Little Sammy, back from the dead," she said teasingly. "And let me guess, you're offering up your own soul?"

"There are a hundred other demons who'd love to get their hands on it. And it's all yours," he ignored her knowing smirk. "All you gotta do if bring Sam back. Give me ten years. Ten years and then you come for me."

"You must be joking," she sighed.

"It's the same deal you give everybody else."

"You're not everybody else," her eyes traveled up and down his body as she stepped closer again. She stretched to her toes so she could rest her chin on the edge of his shoulder, making him look awkwardly to the side to keep her in his line of sight. "Why would I wanna give you anything?"

"Nine years."

"No."

"Eight."

She sighed again, dropping back onto her heels but not moving away, "You keep going, I'll keep saying no."

"Okay, five years," he growled, barely keeping a hold onto his anger. What did this bitch want from him? "Five years, then my bill comes due. That's my last offer. Five years or no deal."

She stared at him, seeming to debate though her eyes – her very human eyes – held an apology. He knew her answer before she even said it, "Then no deal." She began to back away, a small breath of air sounding like "sorry" escaping her lips.

"Fine."

"Fine," she gave one small smile before turning away, heading down the road. He watched her walk slowly away. She said sorry. She wanted to help, but _couldn't. _Did that mean…

"Wait," he stopped her, though she didn't turn. "What do I have to do?"

She visibly sighed this time, her shoulders rising and falling before she turned and came back to him, "First of all, quit groveling. Needy guys are such a turnoff." She paused in thought, "For most women anyways."

She stared up at him, blue eyes soft. He had gotten many looks from many women, but none had ever seemed so understanding. It was almost like she knew what he was going through, had been in his place. He brain grinded to a halt. _Had_ she been in his place? He'd heard demons claim to once have been human. She could have been human once. Maybe she remembered what it was like, losing someone you were close to like he and Sammy were. It would explain why she was being nicer this time around.

"Look," she looked down, unsure. Her voice held none of its usual playfulness, "I shouldn't be doing this. I could get in a lot of trouble. But what can I say? I got a blind spot for you Dean." She took a deep breath and looked up again, directly into his eyes, "I'll do it."

"You'll bring him back?" he clarified.

"I will. And because I'm such a saint, I'll give you one year and one year only. But here's the thing. If you try to welch or weasel your way out, then the deal is off. Sam drops dead, he's back to rotten meat in no time." He jerked back in shock at her words. That was harsh. "So? What do you say?"

Dean stared down into endless pools of blue. He wouldn't get a better offer. This was the only chance he had to save Sammy. It was an easy decision. His hand snapped out, fisting her hair as he brought her forward, bending to place his lips over hers. She stumbled slightly, hands bracing herself on his chest as he deepened the kiss, making sure the deal was completely sealed. Yeah. That's why he stuck his tongue into her mouth. Again.


End file.
